In 1989 I used a payphone next to Madonna. I had just finished college and moved across the country to New York. The city was in the middle of a protracted phone strike. There were no new lines going in, so if I wanted to talk to anyone back home in the Bay Area, I had walk to a corner near Spring and Sixth and drop a handful quarters into the public phone — my ear nearly sprouts fungus at the thought of it now. After spending several weeks in a new city, Madonna’s was the first familiar face I had seen.

I didn’t know anyone. I was a long way from home and I rarely contacted anyone because of the phone strike. It was one of those unique moments in my life when I had the feeling that I could reinvent myself and become anyone.

Over the months, I spent many days and nights just walking the city. New York itself became my best friend. For awhile I was alone and lonely, but eventually I started to establish my new identity, the east coast me — standing clear of subway doors, teaching high school in Crown Heights, scoring a quart of sour pickles at Guss’ on Essex below Delancey. I still remember the first time I walked across the Brooklyn Bridge. I started from the top of the six train steps and ended up three thousand miles from my childhood house, yet as at home as I could be.

This was an era before the internet became an umbilical cord.

If I were a couple decades younger, I’m not sure I could still experience the sense of solitude and liberation I had from the moment I hailed my first cab at JFK. Although I’d still be walking new streets in a different city, I wouldn’t be nearly as alone. I’d be connected to my friends and family. At least in some way, the realtime, social web would anchor me in the same stream of constant status updates and shared photos that enveloped me when I was back home. I’d still have one foot (or at least a couple thumbs) back in the comfort of my digital cocoon.

Two decades after I landed in New York, my nephew is in the throws of making a final choice on which college he will attend. One question he faces is whether he wants to attend school across the country or within an hour of his house. That’s a big question. But I’m not sure it’s nearly as big as it would have been several years ago when there was some truth to the Bruce Springsteen lyric: “When you’re alone you ain’t nothing but alone.”

A question for this era: Is it too much for my nephew to want a few minutes alone with Madonna?

Of course, it’s not just about the big moments that present the potential for self reinvention. It’s about the gradual erosion of moments once set aside for personal introspection — previously solo-drives in your car that are now interrupted by bluetooth conference calls, or waits in bank lines that are consumed by the latest Tweets, or Facebook updates and podcasts joining you at what used to be a lunch table for one.

In the next year or so, I plan to take my family back to New York. The moment I’m most looking forward to is introducing my young son to the New York me as we get off the six train and walk hand in hand across the Brooklyn Bridge. I just hope that someday he has the opportunity to really let go and walk alone across his own bridge.

This post originally appeared in Tweetage Wasteland which has been merged with NextDraft.